The Roommate

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jackie_em
jackie_em
1,565 Followers

I bent over and licked up the outside of her pussy on one side -- never quite touching the lips. I then licked to the outside on the other side. I repeated getting ever closer until I licked up the edge of the labia themselves, first one side then the other. Carrie moaned and thrust her pussy toward my face, but I stayed in control. I avoided actually getting to her clit, but coming ever closer.

As I licked the edges of the lips, they began to spread. I took my tongue and licked just inside the lips on each side, teasing her clit as I got to the top. Carrie moaned louder and grabbed my head. I stuck my tongue as far into her as it would go, then moved up to begin to kiss and suck on her clit. She bucked her hips so hard, I had to work to stay on the bed.

She wrapped her legs around my neck and used her legs to pull me even closer to the wonderful center of her being. At that instant in time, the only thing that mattered, either to Carrie or me was my mouth pleasuring her pussy. She almost pulled out my hair, she was yanking so hard on my head, as she came with shrieks like nothing I'd ever heard from her.

As she came down from her flight of ecstasy, she pulled me up to kiss me, no doubt tasting her pussy on my lips. She brought her hands down and grabbed my ass, then unzipped my skirt. I lifted and she slid my skirt and panties off me, and my cock sprung free for the first time that night.

"Some gay women don't like penetration, but I don't mind."

"You mean you'll let me?"

"As long as I can drive."

She rolled me over on my back, then climbed on me. We kissed and caressed for a while, as I felt my dick sawing between her thighs. She lifted her hips and I could feel the head of my prick slide down her pussy lips a few times, before she reached down and guided in to her tunnel of love. She eased it in slowly, since she was pretty tight, even though she was really wet down there.

She moved her hips back and forth getting it further in each stroke and inch at a time until I was buried deep in her cunt. She paused. Looked me in the eyes and kissed me long and hard before starting a slow steady movement. At that point, I wanted nothing more than to madly fuck this woman, but she was taking her time, and in truth, I wanted her to enjoy it.

Carrie gradually picked up the pace of fucking until she was going at it pretty good. I could feel her pussy tightening around my cock and Carrie moaned and shrieked as she came for the third time, never letting up. I could feel it building up in me, until I grabbed her hips and held her tight to cum deep in her pussy.

As I came down off my orgasm, it occurred to me that I should have used a condom or asked if she was on any kind of birth control. As it turned out, she was on the pill, because she'd been thinking about this for a little while.

"Leigh, I prefer women, but at this point, you're a woman everywhere except between your legs."

"I don't want to change that."

"I won't ask you to, and I won't make any promises, but for now while you're a woman in most ways, we can be lovers."

"You don't know how I've needed something like this, Carrie."

"Out of curiosity, when my father was here, a couple of times, I felt like he hung around for a while after I crashed."

"He did."

"Did my daddy ask things of you?"

"He came into my room, and wanted me to thank him for what he'd done for me."

"I told him to leave you alone, and said you were on your period."

"He never got in my panties, but he wanted other things."

"Just stroke him, or suck him too?"

"He wanted my mouth, and got it, twice."

"And that's not what you wanted."

"Hell, no. But it was easier to do that to get rid of him."

"He's coming back to town in a few weeks."

"Shit."

"I'll tell daddy that you are my lover and my fiancée, and he'd damned well better leave you alone."

"Can I share your bed when he's here?"

"And even regularly until then too."

Carrie kissed me and we made love again before we dropped off to sleep with her spooning me.

...

George came to town, and obviously Carrie talked to him about us before he arrived. He kind of glared at me for a while, before settling down to a quiet dislike. He and I talked as Carrie got ready for the three of us to go to dinner.

"I suppose I should have figured out my daughter was a rug muncher. I just didn't realize you were too."

"Carrie is a big part of the reason I am what I am today."

"I'm the reason you got a good job though."

"And I appreciate it, but I've worked my ass off to earn my place at that company."

"You're a rising star -- or so Brian tells me."

"Star? I don't know about that, but I'm making sure that they don't think I'm just someone riding on who I know."

"Brian actually thanked me for referring you to him."

"Look, I'm not into guys, and I'm not going to thank you anymore the way you seem to like being thanked. But I do appreciate the opportunity you gave me."

"Not only do you have the job I got you, but now my daughter too."

"Carrie is a wonderful woman and I promise you, I'll never do anything to hurt her or betray her trust in me."

"I wish to hell she had found a guy."

"I understand, and were it possible, I'd gladly have been that guy."

"What would you know about being a man?"

"More than you might imagine."

Carrie came out about that time, and we went out. George was gracious at dinner -- you'd hardly have known that he was pissed because he thought his daughter was in a lesbian relationship. Of course, he would be really freaked if he knew what I really was. Then again, I sure as hell wasn't going to tell him. The visit passed and Carrie and my life returned to normal.

...

I had several more presentations to top management, which went as well as my first one. I seemed to be getting a lot of praise from the top brass. I was happy about it even if it wasn't always going over well with my peers. A promotion came up at work, for a manager in a related finance group. Brian told me to apply for it, even though I figured there were a lot more senior and experienced people likely to get the nod before I would. I got the position though, and Brian sat down with me.

"Leigh, you're smart and good, but there's a lot of smart, experienced people here who you've now just jumped past."

"A lot of them aren't going to appreciate this."

"You've got top management support, including my backing, and most of them aren't going to buck that."

"I know you hired me because George asked, but don't understand why you're moving me ahead of more experienced people."

"We've had a diversity problem at this company. We've tried to make the company welcoming to folks like you, but had few in management ranks."

"Folks like me?"

"Let's not play games, Leigh. I'm a senior VP at this place, I make it my business to know what is going on."

"Katherine in HR -- "

"Didn't need to tell me for me to know you're trans."

"You haven't mentioned anything to George?"

"Somehow I don't think he'd take well to knowing his precious daughter has a roommate with a prick, even if you do identify as a woman."

"It's not exactly what you think."

"Look, having an LGBT female in management ranks looks better for us. Seriously, if you were an ordinary guy, you probably wouldn't have been hired, much less given the chance to excel, nor the opportunity for promotion. Play your cards right and in another year, you'll be an AVP."

I couldn't believe it. I had a job, a promotion, and a good chance for further promotions, and it was all predicated on being or seeming to be a woman. Would I ever get a chance to go back to being Leigh, the guy? It didn't look like it.

"Leigh, I know your IDs still show you as male. Just to be smart, and avoid trouble, you need to get them changed to female, even if you never choose to get the surgery."

So now, not only am I dressing as a woman, living as a woman, and working as a woman, I need to be identified as a woman on driver's license and birth certificate. I had some money saved up, and would manage to save more with a promotion, but what good would it do? If I walk away from this and walk away from being a woman, could I even give this place as prior employment?

...

By now, I'd grown out to a b-cup, and Carrie and I were still lovers. She seemed more accepting of the relationship than she'd been initially. I pleased her the way most woman lovers would have, and she was fine with fucking me, as long as she controlled it. I won't say I was happy in my situation, but having a woman lover at least made it tolerable.

For a few minutes I could forget what I'd become and remember what I still had. I might wear skirts, have boobs, look and act like a woman, but I had a cock and a woman to use it on.

I did get my birth certificate and driver's license changed from male to female. Turned out to be good, since I got pulled over for running a red light not long after. Cop looked at my license, checked my record and found I had no moving violations for years, and let me go with a warning. I hate to think what might have happened if my license said male, given how I looked.

I got my promotion to AVP, and shortly after that, Carrie asked me to marry her. We both got white wedding gowns. A few years earlier that thought would have totally appalled me. I let Carrie's parents think my family had disowned me because I turned lesbian. Fact was, I had no intention of ever letting them see me again.

My little sister, Leslie came to town, and I did get with her and told her I had 'changed'. I didn't go into all the details of how or why, but she saw me as I currently present myself. I can't say she was thrilled by it. But she seemed to try to be accepting.

"Leigh, you definitely do not want our folks to see you like this. Dad would shit, and mom would cry."

"I figure I'm better if they just think I hate them, or something."

"I won't say I approve, but if this is what makes you happy, this is what you should do."

"I can't explain why I did it, but it's done and I'm living with it."

"I was surprised, I thought most guys who went female ended up with guys. Is Carrie like you or something?"

"Carrie's all woman, and I'm happy being with her and she's happy with me."

"Well, Leigh, I wish you happiness."

Leslie kissed me on the cheek and left.

Carrie's father walked her down the aisle at our wedding, and as it turned out, Brian walked me down the aisle. I won't ever say this is how I wanted my life to go, but I will say, it could have gone a lot worse. Carrie is pregnant with our baby, though George assumes we used a sperm donor. What is the point of telling him the truth now?

I'm Leigh, the woman, as far as nearly all the world can tell, and I've accepted that.

jackie_em
jackie_em
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cdmonicacdmonicaover 5 years ago
Great story

I love this story. very well written and in line with who I want to be. I am not attracted to men and would love to be with a woman who accepts me as a woman also. I would love to read more about this fabulous couple.

sassysuetvsassysuetvover 5 years ago
Good Story

I really enjoyed this story. I'm very happy that Leigh got to keep her male equipment which continued to function despite the hormone treatments. I'd love to have B-cup sensitive breasts like she ended up with.

Keep up the good work!

cdCindy1cdCindy1over 5 years ago
interesting story

I really enjoyed reading this story. It went in a different direction than I thought it would but in the end it felt right. I'm a crossdresser and if it was me I'd let George fuck my man-pussy after I sucked him dry -- but that's me. Ending up with Carrie as a lover and a wife is the perfect ending for Leigh.

Thanks for writing this story. Please write more like it.

Hugs & kisses,

cdCindy1

AnonymousAnonymousalmost 6 years ago
Great.

one of the best story i have read here.

Very good job.

Thank you.

AnonymousAnonymousalmost 6 years ago

please do a second chapter i have read this twice and love it

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